Water → HCID 69969505、化合物

HRID 1937743ノート

反応式

HRID 1937743 の反応式
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[C@H:10]([OH:15])[C@@H:9]([NH:16][C:17](=[O:25])[C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[C:8]=2[CH:26]=1)(=[O:3])[CH3:2].O.FC(F)(F)C(O)=[O:31].FC(F)(F)C(OI(C1C=CC=CC=1)OC(=O)C(F)(F)F)=O>C(#N)C>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:17]([NH:16][C@H:9]2[C:8]3[CH:26]=[C:4]([C:1](=[O:3])[CH2:2][OH:31])[CH:5]=[CH:6][C:7]=3[O:12][C:11]([CH3:14])([CH3:13])[C@@H:10]2[OH:15])=[O:25])=[CH:19][CH:20]=1

参加物

6

反応物 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 193943Carabersat

生成物 1

HCID 69969505HCID 69969505、化合物収率 24%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

(3R,4S)-6-Acetyl-4-(4-fluorobenzamido)-3,4-dihydro-2,2-dimethyl-3-hydroxy-2H-1-benzopyran D5 (1.83 g, 5.0 mmol) (Example 20 of WO92/22293) was dissolved in acetonitrile (25 ml), water (5 ml) and trifluoroacetic acid (0.77 ml, 10.0 mmol). [Bis(trifluoroacetoxy)iodo]benzene (4.30 g, 10.0 mmol) was added and the reaction stirred under reflux for three hours. The reaction mixture was allowed to cool and the acetonitrile was removed in vacuo, the resulting material being partitioned between water (50 ml) and dichloromethane (125 ml). The aqueous layer was extracted with further portions of dichloromethane (3×25 ml) and the combined organic extracts were dried over magnesium sulphate, filtered and the solvent removed in vacuo. The resulting yellow foam was purified by column chromatography on silica, eluting with 20% to 50% ethyl acetate in hexane to afford the title compound as a white solid (0.44 g, 24%), m.p. 216° C.

後処理

  1. temperatureunder reflux for three hours
  2. temperatureto cool
  3. customthe acetonitrile was removed in vacuo
  4. customthe resulting material being partitioned between water (50 ml) and dichloromethane (125 ml)
  5. extractionThe aqueous layer was extracted with further portions of dichloromethane (3×25 ml)
  6. dry with materialthe combined organic extracts were dried over magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customThe resulting yellow foam was purified by column chromatography on silica
  10. washeluting with 20% to 50% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-327578b0d2f648d58c7dfcc8427d5874
出典データセット
uspto-grants-2002_05
特許番号
US06395909B1

反応ノート

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